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Vacation rentals in Peekskill

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Top-rated vacation rentals in Peekskill

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Cottage in Cortlandt

4.99 out of 5 average rating, 167 reviews

The Little Cottage in the Woods

The Little Cottage in the Woods Nestled among the trees, and in close proximity to our main house, this studio cottage is newly refurbished, very private and is in a great location to access the Hudson Valley. Hiking trails are within minutes of the cottage or right out the front door. Golf courses are also minutes away. Whether you are in the area on business or just looking to escape for the weekend and enjoy the out doors. It is situated on 9 1/2 hikeable acres, all available to our guests

Rental unit in Philipstown

4.89 out of 5 average rating, 202 reviews

Foxglove Farm

Peace and tranquility await you at the end of this private road surrounded by forest. My home is a log cabin with a private apartment on the lower level, which includes a patio as well as use of other outdoor spaces. There is a fire pit just past your patio and a short path will put you on the Appalachian Trail. As an herbalist and ethnobotanist, plants are my love and my livelihood. They are an integral part of my life and my home. I welcome you to stroll through the many gardens and paths.

Rental unit in Peekskill

4.8 out of 5 average rating, 127 reviews

Little haven by the woods

This is a walk-out basement with two private entrances, and it’s own private outside area. The patio has comfy furniture with a bbq. The kitchen is small, yet efficient with large windows. The bedroom is cozy and comfy with a large smart tv on the wall. The bedroom has a 3/4 wall dividing it from the rest of the apt, but no actual door. So it could be considered a “studio”. We are steps from the trail heads into Blue Mt park. We’re also walking distance to the metro north & downtown.

Guest suite in Croton-on-Hudson

4.81 out of 5 average rating, 120 reviews

Cozy one-bedroom suite within a house

This one-bedroom suite (lower level, sun-filled apartment with keyed door) within a house is a tranquil oasis waiting to welcome you. Surrounded by nature, directly across from a brook, it is walking distance from Oscawana Park and hiking trails -- you will leave feeling refreshed and inspired. A short drive from NYC, and convenient to public transportion, this peaceful property is a ten-minute drive from the historic Croton Dam, Croton village, and Croton Point waterfront park.

Home in Cold Spring

4.95 out of 5 average rating, 155 reviews

Cozy, Modern Retreat in the Woods of Cold Spring

Newly renovated with modern style and amenities yet retaining all of its rustic warmth and charm, our home is perfect for your next get away. Outdoors, enjoy the salt water pool, patio, grill and fire pit in our secluded setting. Indoors we offer a sauna, steam shower, central heat and air, a woodburning fire place, ping pong table, washer and dryer, and a fully loaded kitchen. Located 7 minutes drive from charming Cold Spring and just across the river from West Point.

Home in Peekskill

4.9 out of 5 average rating, 162 reviews

The Peekskill RiverView House

The Peekskill RiverView House A fully renovated dream house overlooking the historic Peekskill Bay. This 3 bedroom 3.5 bath designer house is a 5 minute walk to the train station as well as the historic downtown. It’s truly the gateway to the Hudson Valley along with having the walkable access to culture, hiking, biking, culinary, spa, and entertainment activities within City limits. Expansive decks on all 3 floors with spectacular Hudson River views from every room.

Guesthouse in Cold Spring

4.99 out of 5 average rating, 108 reviews

Modern/bright forest escape. Near village & train

Modern, efficiently and elegantly constructed private flexible garden apt. guesthouse can be used as a studio apartment, or as a private personal retreat space for art/work/rest/meditation. Hiking trails available right out the door, and just a few minutes walk to Cold Spring's vibrant Main Street and Metro North train station. Comfortable bed, all modern amenities. Private patio. Native pollinator gardens surround. Solar orientation brings in natural sunlight.

Guesthouse in Mahopac

4.93 out of 5 average rating, 135 reviews

Sunny Lakeview Guesthouse

Art and light filled spacious studio with panoramic views overlooking lake Mahopac perched on a steep hill. Walkable to swimming/paddleboarding/canoeing. Many fine restaurants or casual takeout options, and boasting an excellent coffee shop. Train ride from Grand Central to Croton Falls, then a 12 minute drive or shuttle ride. Close to Fahenstock Park, Cold Springs, Beacon, Ridgefield, or walk up the hill to the trails of Volz park

Guest suite in Haverstraw

4.95 out of 5 average rating, 313 reviews

Haverstraw Hospitality Suite

Quiet & cozy suite, with a comfortable full bed & private bathroom in newly renovated garden (basement) level of a single-family home. WiFi/air conditioning & heat unit/FiOS cable - roku TV. Coffee/tea available. Rollaway available for an extra bed. The neighborhood is quiet, and parking is available in the driveway. Feel free to come and go as you please -- we hope our guests feel like this is their home away from home:)

Rental unit in Croton-on-Hudson

4.98 out of 5 average rating, 292 reviews

Luxury 2bd⭐Comfort+Style⭐

45 min train to Grand Central. Apt is 1.9mi to train, supermarket. Free PARKING. Two 4K TVs, 4K Blu-ray library, NFLX/AMZN/HBO/Apple TV. XBOX 1X. Fast WIFI. SS APPL, stocked kitchen. Bd1: adjustable queen, 50" 4K TV. Bd2: adj queen. Office area (desk, fast wifi), private porch. Sidewalks. 7 min walk to cafes, a bar, and restaurants. Car rental is 16 min walk. Hiking, kayaking. I LIVE NEARBY IN ANOTHER APT | $75 PET FEE |

Rental unit in Beacon

4.99 out of 5 average rating, 505 reviews

Rustic Spa Retreat

10 minute walk to Main Street (many restaurants, cafes, galleries, etc) 10 minute walk to Mt Beacon TrailHead. (It's not a hotel and not on Main Street: it's in a residential neighborhood) Cozy, small space set up for a couple (or solo traveler) looking for a relaxing short escape from "The Real World". A couple days here really feels likes so much longer (especially if you take a steam and a jacuzzi)!

Guesthouse in Peekskill

4.94 out of 5 average rating, 221 reviews

Peekskill Carriage House Downtown Studio

Located close to the center of town, this is the perfect launchpad to experience local restaurants, coffee houses, the Paramount Theater, shopping, etc. and a short drive to stunning hikes, the Hudson Valley and beyond. The apartment is ideal for one or two and features a kitchenette, bathroom, dining island, comfortable queen bed, and couch. peekskillcarriagehouse.com

Vacation rentals for every style

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Unique stays

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Popular amenities for Peekskill vacation rentals

Free parking on premises

Air conditioning

Stay near Peekskill's top sights

Stop & Shop9 locals recommend

Blue Mountain Park4 locals recommend

Paramount Hudson Valley Theater16 locals recommend

Spins Hudson8 locals recommend

The Peekskill Coffee House15 locals recommend

Birdsall House19 locals recommend

Other great vacation rentals in Peekskill

Guest suite in Croton-on-Hudson

4.99 out of 5 average rating, 109 reviews

Enchanting Farmhouse Suite w/ pool and sauna

Loft in Cornwall

4.85 out of 5 average rating, 421 reviews

Country Getaway - Close to Hiking & Storm King

Rental unit in Newburgh

4.95 out of 5 average rating, 132 reviews

Ela - a 1 Bed Escape, Washer/Dryer in Unit

Cottage in Philipstown

4.99 out of 5 average rating, 183 reviews

Modern Country Cottage by Bear Mountain

Rental unit in Beacon

4.93 out of 5 average rating, 105 reviews

Cozy Studio with Backyard, Central Air

Cottage in Greenwood Lake

4.93 out of 5 average rating, 151 reviews

Cozy home in the Village of Greenwood Lake

Home in Peekskill

5 out of 5 average rating, 28 reviews

Charming Home in Peekskill NY

Rental unit in Cortlandt

4.8 out of 5 average rating, 41 reviews

Peaceful Hideaway

Quick stats about vacation rentals in Peekskill

Total rentals
20 properties
Total number of reviews
1.4K reviews
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
Local attractions
Blue Mountain Park, Paramount Hudson Valley Theater, and Table 9

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Peekskill?
Yes! Work meets play with ease at over 10 vacation rentals in Peekskill featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in house rentals in Peekskill?
Experience the best of Peekskill with our house rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
What are the most popular amenities for House Rentals in Peekskill?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with a kitchen, over 10 homes with wifi, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Peekskill have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Peekskill. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Peekskill have free parking?
Absolutely! We offer over 10 house rentals with free parking in Peekskill. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Peekskill have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Peekskill. Enjoy a tailored experience with all the comforts you desire.

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